As much as he can

Coming from Vermont, I can say Bernie has always been a do what you say type of politician. I know it's rare and hard for many people to believe, but he really does do what he believes is right. That doesn't mean I agree with him on everything--guns anyone--but I at least know that he stands behind what he believes and won't be bought of swayed. Does this mean he will be perfect? I don't think there's ever been a perfect leader, political or otherwise. Even MLK Jr. And Gandhi had their faults, just as we all do. But he'd really try to follow his convictions, and that's more than I can say for the others.

No, but in his defense,

How many elected officials have ever followed through on all of their campaign promises? It seems to have become an accepted practice now that politicians don't really mean anything they say in an election year. The times of picking the best candidate have come and gone, and now we as a society just try not to pick the worst one.

Cutting military doesn't give endless money.

Right now we are losing money each year, we could cut military spending by 700 billion, with that you could probably spend 400 mil and keep debt going down. His ideas of free college and loss of student debt would take up almost 300 billion of that. With his other spending ideas he would end up paying much more than he can. His ideas are much like Cuba where he would give everyone free stuff but everyone would make the same based of hours worked. This would bring average income down far, not as far as Cuba (20$/month) but far enough that we would face massive poverty. This would end up causing a lack of money off income tax that the gov would receive sending the US into terrible debt. His ideas will not allow him to do what he promises.

There's is a small chance of things working out as intended or working out at all

While his promises are decent and his record (as far as we know despite suspicions of embezzlement in his campaign and the fact that he never really passed a bill of significance).

For starters, we can all scrap the ideas of conventionally passing any of his major reforms considering his first 2 years will be dealing with a majority-republican establishment that will constantly attack him along with a democrat party and entire system dedicated to an ineffective presidency under his administration.

We can then scrap any amendment of the constitution considering that would require consent from all the republican, democrat, and universally bought-out states and congress and senate.

Supreme court cannot override anyone (even if he chooses his court) unless it goes against the constitution. Money in politics and private campaign financing are perfectly fine in the constitution as is electoral college. Which eliminates an entire chunk of his platform right there.

Third, executive actions only last 90 or so days and - while being his only real hope of doing anything - and probably can/will lead to impeachment should he commit too many orders.